tert-Butyl bromoacetate → HCID 53998528, compound

HRID 1252228Notes

Reaction equation

HRID 1252228 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:17][CH2:16][CH:15]([SH:18])[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].N12CCCN=C1CCCCC2>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:17][CH2:16][CH:15]([S:18][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:14][CH2:13]2)=[O:11])=[CH:19][CH:20]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13292713(4-Nitrophenyl)methyl 4-sulfanylpiperidine-1-carboxylate

Product 1

HCID 53998528HCID 53998528, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-p-nitrobenzyloxycarbonyl-4-mercaptopiperidine (1.19 g), t-butyl bromoacetate (780 mg) and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) (608 mg) in benzene (10 ml) was stirred for 5 minutes under nitrogen atmosphere. The reaction mixture was washed successively with water, dilute hydrochloric acid and water, dried over anhydrous sodium sulfate and evaporated to give 1-p-nitrobenzyloxycarbonyl-4-t-butoxycarbonylmethylthiopiperidine.

Workup

  1. washThe reaction mixture was washed successively with water, dilute hydrochloric acid and water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-080a330fa9894725830a72ea7a2a028f
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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